The pharmaceutically active compound 1-(4-Methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl-acetic acid (“Compound A”) is an antagonist of the G-protein coupled chemokine receptor homologous molecule expressed on Th2 lymphocytes (“CRTh2”) that is useful for the treatment of several disorders such as asthma and atopic dermatitis. Compound A has the following chemical structure:
[1-(4-Methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid
Compound A, methods of synthesizing Compound A and methods of treating various disorders using Compound A are referred to in U.S. Pat. No. 7,666,878 which issued on May 10, 2011, the contents of which are herein incorporated by reference in its entirety.
Although methods of producing Compound A are known, as set forth, for example, in PCT/IB2016/05577, and the above referenced patent, the present invention discloses for the first time a method of producing Compound A which has fewer steps, has a higher yield, and has a higher selectivity for Compound A. The invention accomplishes these features primarily via the use of an aza-indo-3-yl acetic acid derivative intermediate which is described in more detail below. The advantages described above are exemplified in the examples that follow.